Trusted Advisory Services

Mergers and Acquisitions, Executive Coaching, Strategic Business Consultation

Helping top performing leaders navigate challenging seasons, solve difficult problems, gain clarity on complex issues and achieve big goals in the face of tough odds for over 35 years.

ABOUT

Supporting smart, ambitious, ethical leaders in achieving personal and professional prosperity (in the fullest meaning of the word) brings me great satisfaction. 

I am an entrepreneur, mergers and acquisitions advisor, and executive coach to high capacity business leaders.

I have founded, bought and sold multiple companies for my own account. As an investment banker, I’ve evaluated over 5,000 businesses over the last 35 years in about every industry conceivable; and provided mergers and acquisitions advisory services for approximately half a billion dollars in business sales involving hundreds of companies.

I serve as an executive coach to extremely successful business leaders, many in the top 1% of income earners in the United States. As a 10x Catalyst Group chair and Vistage Chair, I currently facilitate five peer advisory groups of approximately 60 high capacity CEOs and business leaders.

I’ve published two #1 bestselling books. My most recent is “Finish Strong - Exit Well” which helps entrepreneurs prepare, position and sell their businesses for top dollar.

I am deeply involved in our Central Oregon community, as a member and past president of Rotary Club of Greater Bend, as producer of the annual Central Oregon Leaders Prayer Breakfast (largest in the state), the annual Excellerate Business Forum, which draws hundreds of business leaders representing about $4 Billion in annual revenue, and the annual Bend Christmas Parade (largest in the state).

I’m an ex-Army Ranger Captain, black belt martial artist, avid fly fisherman, whitewater enthusiast and outdoor adventure lover.

Founder and President

SALES, MERGERS, ACQUISITIONS, STRATEGIC BUSINESS DEVELOPMENT

Helping entrepreneurs buy, build, prepare, position and sell quality companies for over 35 years.

CrossPointe is a business advisory firm focused on serving privately held companies with annual revenues from $1,000,000 to $50,000,000. Our main services are:

  • Seller Representation

  • Selective Acquisition Search Projects

  • Positioning and Preparing Businesses for Optimal Exit​​

  • Executive Coaching and Consulting

PORTFOLIO OF SERVICES

Founder and President

CHRISTIAN ENTREPRENEURS AND CEOs

SMALL BUSINESS. BIG MISSION.™

Business leaders of faith, with God given ambition and self-made business expertise gather at 10x. Sharing His blessings and our business growth leads to exponential success in life, professionally and spiritually.

  • 4 Dedicated Invitation-Only Groups

  • 48+ Business Leaders of Christian Faith

  • $120M in 10x Inspired Profits Generated

Chairman, Vistage Int’l 667

CEO COACHING & PEER ADVISORY PROGRAM

BETTER LEADERS. BETTER DECISIONS. BETTER RESULTS.

Vistage is the world’s largest CEO coaching and peer advisory organization for small and midsize business leaders. We offer the most effective approach to achieve better business results, grow your company faster and maximize your impact as a leader.

For more than 65 years, Vistage has helped CEOs, business owners and key executives reach new levels of success.

  • “I have known Michael Sipe for more than 20 years. He recently helped my partners and me sell our manufacturing business. We found Mike to be a quick study of our business, extremely knowledgeable in helping us prepare for the sales process and then leading the actual process of selling our business. His book pulls together his years of experience helping business owners walk the journey of building their company, preparing it for sale, and then leading the sales process. His advice and counsel are invaluable to business owners and his tools are detailed in Finish Strong – Exit Well.”

    Jon D. Tompkins

    Retired CEO/Chairman KLA-Tencor and

    CEO Spectra-Physics

  • “In the dynamic arena of business transactions, where the stakes are high and the margins for error slim, Michael Sipe's Finish Strong – Exit Well emerges as a beacon of strategic wisdom and practical guidance. This book is a masterclass in the art of preparation, positioning, and execution for achieving top dollar outcomes.”

    Patricia Fripp

    Presentation Skills Expert, Executive Speech Coach,

    and Co-Author of Deliver Unforgettable Presentations

  • “I have practiced corporate M&A for over 35 years, handling transactions ranging in size from a few million dollars to hundreds of millions of dollars. What is most noteworthy about Michael Sipe is his creativity in problem solving when the inevitable transaction obstacles arise. It is always rewarding to watch Mike work his magic.”

    Gregory P. O’Hara
    Partner, Nixon Peabody, LLP, Selected for

    inclusion in The Best Lawyers in America 2023

  • “I understand deals. As the past national president of the National Association of Women Business Owners, the owner of an internationally known business, and a business attorney, I’ve been involved in well over 1,000 transactions in my career. With that background, you might wonder why my family and I retained Michael Sipe and CrossPointe to advise and assist us in four transactions: two acquisitions and two divestitures. CrossPointe has the ability to bring quality buyers and sellers to the table. Mike can get deals done quickly under optimum terms. He has a talent for working a deal through the inevitable bumps and bringing it to closure smoothly and amicably. One of the hidden benefits of his firm's comprehensive services, but perhaps one of the most important, is that by turning the transaction process over to them to manage, I can focus on running my business most effectively, with minimal distraction. At the end of the deal, my overall profit is higher, because I’ve been able to maximize my business performance as well as complete a successful transaction quickly.”

    Margaret A. Smith

    President, Lifestyle Los Gatos Inc. 

  • "As a merger and acquisitions attorney, I know that in order to properly serve clients a business Intermediary must have a wide variety of skills including knowledge of the accounting, legal, tax, deal-making, and psychological issues involved in a transaction. The Intermediary must be proactive, an excellent communicator, and able to work well with his client’s lawyers and accountants. Michael Sipe excels in all these areas and I give him the highest recommendation!”

    James C. Chapman

    Rimon Law, Partner: Emerging Companies and Venture Capital

  • "Your frankness, persistence, hard work, and diligence paid off for my client. I respect your knowledge and abilities dealing with people. I commend you on your devotion to the cause. Your marketing methods are excellent, professional, and put forth a presentation of the company that generated interest from qualified potential buyers. I am confident that had we selected any of the other brokers we interviewed, the results achieved would not have been as successful and I am not confident we would have made a deal. You have our thanks and backing for the asking, because you proved yourself by results. We miss the daily emails and communication that became part of the process as you led us through the negotiation maze. You are a good person, a professional and competent businessman, and a pleasure to work with, and we are thankful our paths came together for the benefit of my client and the successful attainment of our goal. Thank you."

    Joe Winchell, CPA, and

    Patricia D. Masciana, Former President and Owner, Acroscope Inc. 

  • “I am a transactional attorney with a regional practice and have had the pleasure of working with Michael Sipe as an Intermediary and consultant on deals of various sizes. I am consistently impressed with his ability to navigate both the relationship between buyers and sellers and all of the multifaceted components of complex transactions, including deal structures, financial analysis, and strategy. I have found Michael to be exceptionally effective at getting a deal over the finish line but also knowing when to go back to the drawing board. It’s always a pleasure working with Mike.”

    Jennilyn K. Aston

    Lynch Murphy McLane LLP, Bend, Oregon

  • "The highest compliment we can give Michael Sipe and CrossPointe is at the personal level. We could elaborate on the ultimate skills Mike brings to the buying/selling process; the alacrity with which he understands the technical details of the business; the depth, accuracy, and volume of presentation, which sets him apart from all others; the careful search and selection of buyers; the fearless interaction, even confrontation, with potential buyers whose motives or situations are questionable; the total understanding and presentation of the financial projections and conditions of the business; the development of a good and fair selling price; the ability to forge a solid alliance between buyer and seller . . . we could go on. Mike brings such a high degree of professional integrity, honesty, and intense involvement that after all the cards have been played and the game is over, EVERYONE is a winner, and new friendships have been created."

    Maynard Kuljian

    retired CEO, Neilsen-Kuljian Inc.

  • “I've had the privilege of collaborating with Michael Sipe over the last two decades. In addition to advising me through the buyout of my partner, his business development coaching has been instrumental in elevating my business, and also the businesses of many of my colleagues. Thank you, Mike, for sharing your wisdom and providing this valuable resource for enhancing business value and fostering a business owner’s growth.”

    Barrett Scott

    CEO, Stock & Option Solutions

  • “In my previous private law practice, I have had the pleasure of working with Mike on several transactions requiring creative problem-solving. Not only does Mike spend time getting to know all parties involved, he understands where potential deal issues arise within each sector. He is knowledgeable, experienced, and tenacious in his pursuit of identifying solutions to complex challenges. His ability to add value to a transaction is exceptional.”

    Heather Hansen

    Vice President and General Counsel, Bend Oregon

  • “I leaned on Michael Sipe for the two most pivotal moments in my 40-year career. Mike represented us as we acquired our biggest competitor launching a 15X growth trajectory unparalleled in our industry. Last year I relied on Mike’s knowledge and integrity to “exit well” as I sold my company to my partners in a deeply satisfying transaction. It is great to see his knowledge available for everyone in his new book, Finish Strong – Exit Well.

    Stan Vuckovich

    Retired CEO, KBM Hogue

  • “I have known Michael Sipe for many years. That's why, when the time came to sell the company my partners and I built over more than 30 years, he was the one we trusted. He quickly learned the nuances of our industry and offered sage advice and a thoughtful perspective, which proved to be extremely valuable. Watching him employ what he calls his “invisible negotiating” strategies while dealing with very sophisticated buyers was fascinating . . . and very successful!”

    David Payne

    Ex-CEO, Splash! Events Inc.

  • “I worked with Michael Sipe on a sale that stalled, but which we then successfully completed a couple of years later with the same buyer. Mike always carried a calm and collected demeanor, which was extremely critical to help me stay focused on only the most important things. Mike is professional, strategic, and experienced, with a very high level of personal integrity. Above all these, he genuinely cares! I was very fortunate to have Mike guide me through the whole selling process.”

    Angie Wong

    Retired CEO, Ojo Technology Inc. 

  • “This book is a game-changer! Michael Sipe's guidance has been instrumental in shaping our business journey, transforming our ideas into tangible success. With innovative exercises, Sipe ignited a spark within us, propelling our tech business to unprecedented heights. A must-read for any entrepreneur aiming to build, scale, and eventually sell a thriving business.”

    James Kramer

    Founder and CEO, Commissioned

  • “Michael Sipe has been instrumental in all phases of our business journey and success story. He was the agent that brought us our first company, then presented an additional company in the same space, provided real-time operating guidance and expertise to grow the business, and then guided us through a successful sale. His methods are tried and true.”

    Rick Hetherington

    Retired CEO, M2LR Inc.

  • “I’ve known Mike both professionally and personally for 30 years and he’s a wealth of both experience and wisdom. As is the case with most things in life, when you walk down the deal trail it pays to have a guide with sufficient “trail dust” on him, and Mike has that. This book distills his decades of advisory guidance—a must-read before you hit the trail.”

    Brandt Brereton

    General Partner, Perpetuate Capital

  • “After less than one year of applying the business-building wisdom I learned in working with Michael Sipe and CrossPointe, my company's revenue increased by almost 75 percent. That in itself sells the power of the strategies in this book. I am one of the most skeptical, “show me the proof” kinds of people out there and I made the mistake of putting off working with Mike for almost four years. Call it God's timing, or better late than never, but it has been the best decision I have ever made in my 20+ years of leadership.”

    Robert W. Bennington

    CEO/Owner, Bennington Properties

Inviting Your Connection

Discover how we can support your goals and drive meaningful results. Book a time to discuss your needs, explore solutions, and evaluate how we can work together for success.

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Let's Connect and Explore Possibilities

We invite a conversation with you! Whether you're exploring new opportunities, considering strategies for exit, discussing potential collaborations, investigating solutions, or looking to grow and build enterprise value, we can help, or we likely know those who can.

Let's connect to exchange ideas, uncover possibilities, and discover ways we can create mutual value. Reach out today—we’re excited to hear from you!